Gay Crossdresser Stories

GayDemon's Stories: On this page you can find erotic fiction where you can read about men dressing up as women and gay sex with transvestites and crossdressers.

Cross dresser.. Twink.. Tranny?

By djfmonkey 22 Dec 2021

My straight buddy and I visit a gay bar, where we discover our own inner selves, and the truth about each other

9.3 (166) 8336 8 Min Comments

Shower Power

By BillyBoy 22 Dec 2021

'Daddy' shaved me in the shower. While the water was pouring over us, he put me in a matching set of rubbery vintage Playtex bra and open bottom girdle panties.

8.4 (14) 2221 3 Min Comments

Chis(topher) & Chris(tina) (ch. 3)

By djfmonkey 12 Dec 2021

Chris and I finally visit my parents for the holidays in my overly homophobic upstate New York Hometown

9.6 (119) 2314 11 Min Comments

Secret Sissy

By BillyBoy 10 Dec 2021

I've been in the closet all my life. Finally, I have a chance to try out being a sissy girl for a real man

7.4 (12) 4808 5 Min Comments

Dreams and Frustration

By BillyBoy 9 Dec 2021

Every day I awake from a dream of being used as a girl whore. I can't stop it. I'm in trouble!

7.9 (12) 2715 5 Min Comments

My secret dreams

By BillyBoy 7 Dec 2021

The gay date I'd love to experience. I've had a few gay experiences, but someday a man will make me his little bitch. I'd love that!

8.3 (9) 1747 2 Min Comments

Halloween party

By BillyBoy 2 Dec 2021

I finally let him seduce me. I agree to meet him. He has been flirting and making promises. Then at the last minute, he tells me I'm going to dress like a woman tonight.

8.1 (18) 4464 3 Min Comments

Park Slut (ch. 3)

By Alleykat 30 Nov 2021

Turned into the park cocksucker by a fat old man

8.9 (28) 4203 7 Min Comments

Jessi’s debut - A true Jessi story

By JohnRain24601 25 Nov 2021

John goes out as Jessi for the first time - to a party at an adult book store.

8.3 (11) 653 14 Min Comments

Chis(topher) & Chris(tina) (ch. 2)

By djfmonkey 23 Nov 2021

Chapter 2. - Chris and I meet the grandparents

9.7 (116) 2066 5 Min Comments

Park Slut (ch. 3)

By Alleykat 23 Nov 2021

I would go to the park at night letting guys blow me until the fat old man turned me into the cocksucking cumloving slut at the park and at my mom's house.

9.0 (38) 5474 5 Min Comments

Chis(topher) & Chris(tina)

By djfmonkey 22 Nov 2021

I met and fell for a crossdresser, explore chapter 1 introducing us, and future chapters meeting family and friends

9.3 (127) 4405 9 Min Comments

Now I'm a crossdressing Domme?

By BillyBoy 20 Nov 2021

A shy, submissive guy hits me up to dress like his wife and Domme him. I actually liked it more than I thought I would!

8.7 (11) 1795 4 Min Comments

How this straight guy became a sissy bottom

By Somewhat Straight 17 Nov 2021

It took while, but my transformation is complete

8.4 (355) 76412 9 Min Comments

Doctors are human too

By BillyBoy 11 Nov 2021

I forgot and wore some panties to my check-up. The doc was surprised. But he responded differently than I expected.

8.3 (45) 8379 6 Min Comments

blow and go buddy gets kinky

By BillyBoy 10 Nov 2021

Joe was always pretty much a Dom. But he seemed to figure out I'd do pretty much anything to suck him off. So he just keeps pushing. Now I have to go out and buy some items he requested. And that is a whole other story!

9.2 (37) 3223 6 Min Comments

In a short span I became a sissy boy trap (ch. 2)

By Desertbiguy 10 Nov 2021

I had spent all of my time getting indoctrinated in gay sex by Tom G. I forgot about my first man to pop my anal cherry Mark.

8.1 (22) 2998 3 Min Comments

Introduction into Gay Domination (ch. 2)

By Anthony 8 Nov 2021

I went to work and tried not to run into Jerry, but that was hard, seemed like Jerry kept looking over at me and would walk by me giving me a look. When no one was around, he would come up to me and show me a picture of me on his phone of me in one of the positions that I was in.

8.4 (23) 2735 4 Min Comments

Tranny at the bar

By djfmonkey 8 Nov 2021

The best looking girl in the bar was a guy and I love her.

9.3 (174) 10480 10 Min Comments

Nanny cam gone bad

By BillyBoy 5 Nov 2021

My wife installed one of those nanny cams. She wanted to see what the dog was doing when we were at work. She didn't tell me. She started watching me dress in her underclothes and tie myself up like a kidnap victim, jerking off. Not sure what to do, she asked a friend to watch the videos. He knew just what to do with me.

8.4 (13) 2266 7 Min Comments

Crossdressing

By BillyBoy 2 Nov 2021

Envious of the girls always getting to wear those cute little bras and panties.

8.5 (19) 4715 10 Min Comments

Halloween is a great time to express sexual feelings

By Desertbiguy 2 Nov 2021

I decided to dress up as a girl for halloween. There was a big party going on for us jr high kids. And looked good. Maybe to good. Mark was a good looking guy. Something happened at party. He became attracted to me.

9.0 (60) 4230 4 Min Comments

Becoming the Fishing Camp Princess

By Dickguy4U2 31 Oct 2021

While well over the legal age of sexual consent, my looks represented a much different picture. Broght up by a single parent overbearing mother, my being raised was far from the normal channels of a lone single male son.With mom making dresses and me the perfect slender size to model her creations, I guess you could say that the soft silk and lace never failed to stimulate me in a secret sexy way

8.8 (54) 6906 24 Min Comments

A Halloween story

By BillyBoy 28 Oct 2021

Dressed up for Halloween and nowhere to go. Until I get invited to a last-minute party.

8.8 (48) 15066 7 Min Comments

Macy's gay parade

By BillyBoy 23 Oct 2021

The clerk at Macy's gave me a strange look as he checked out the lingerie I was buying.

9.2 (18) 2283 5 Min Comments

Prom night for a sissy crossdresser

By BillyBoy 19 Oct 2021

I meet a cute sissy out for prom night. But he needs a date.

8.1 (27) 3320 4 Min Comments

Getting fucked by grinder date in hotel

By zeenatcd 18 Oct 2021

I met one mature men on grindr and and then we enjoyed a lot in hotel room. He fucked my 2 times in row continuously. Then he became my fantasy partner.

8.5 (23) 7378 7 Min Comments

The crossdresser

By BillyBoy 16 Oct 2021

Silly me gets seduced by a pretty closet crossdresser. I help her come out, so to speak. And I have a nice time as well.

9.0 (14) 2146 5 Min Comments

working my way up to a complete sissy tramp

By BillyBoy 13 Oct 2021

A pervert friend takes me from my first hand-job, up through the progression to where I was escorting him out to bars as a woman.

8.6 (18) 1804 10 Min Comments

scary trying to be yourself

By BillyBoy 12 Oct 2021

I thought wearing my sister's underwear made me gay. I was worried about that. But it didn't. But finding someone who wasn't repulsed seeing me in her stuff was very difficult. Until now.

7.2 (6) 611 9 Min Comments

I'm a gay sissy transgender fuck toy

By BillyBoy 9 Oct 2021

When I came back from California, changed into a Caitlyn, I was surprised how many of my old schoolmates and teachers were trying to get in touch.

8.3 (24) 4227 7 Min Comments

I married a fat girl

By BillyBoy 8 Oct 2021

I only found out much later that she set me up to catch me in her undies and tricked me into becoming a sissy peg boy and later a slut for her x boyfriend who she was still fucking. I guess that is the whole story, actually!

8.4 (20) 4767 6 Min Comments

first time caught in hers

By BillyBoy 6 Oct 2021

Wife catches me the first time. Very embarassing. But not at all as bad as when she turns me over to the kinky gay guy she works with.

8.7 (29) 5359 10 Min Comments

diapered like a helpless bitch

By BillyBoy 5 Oct 2021

Joe found my personal chats and used them to blackmail and abuse me. I loved it!

8.0 (28) 12984 4 Min Comments

An interactive fantasy game

By BillyBoy 1 Oct 2021

Going to a hotel dating game is different when all the people are matched up to their kinky fetishes and fantasies.

8.2 (20) 2886 8 Min Comments